Few things are more American than the open highway, and with sun-soaked boulevards, winding coastline, and eclectic and exciting discoveries awaiting from one town to the next, is there a better place for a road trip than Southern California? Starting in the dreamy beach town of Santa Monica, you can go on an overland journey to discover the timeless architecture and otherworldly landscape of the surrounding desert, then return to the big city to sample some of the buzziest beach clubs and restaurants on offer anywhere. From the historic and trendy to casual and chic, planning an automotive adventure allows travelers to explore the region at their own pace while proving just how diverse—and incredible—California can be.
Shop and eat in Santa Monica
Santa Monica at sunset
Courtesy of Visit Los Angeles/Max Whittaker
Hardly 30 minutes from Los Angeles International Airport, Santa Monica continues to reinvent itself as a top destination for a laid-back beachside way of life. You can find this coastal casual style among the lively boutiques on Montana Avenue. Shop for those casual-chic looks when staying at a beachside suite at Oceana Santa Monica, a resort with an enviable location and extraordinary experiences, like a private ride over Malibu by helicopter. Of course, you can also simply sip a craft aperitivo by the pool. Santa Monica is also an excellent place for low-key, delicious eating, and Rustic Canyon delivers hyper-seasonal California cuisine emblematic of the town’s forward-thinking spirit.
Book a VIP tour of the Petersen Automotive Museum
A look inside the Petersen Automotive Museum’s renowned collection.
Courtesy of Visit California/Max Whittaker
The Petersen Automotive Museum is already a must-visit, boasting one of the planet’s largest and most valuable car collections. Yet true auto aficionados can kick things into another gear altogether with a private VIP experience that includes transportation to and from the museum in a vehicle from the collection, plus after-hours access to the exhibit (and its private subterranean vault) guided by one of the museum’s historians.
Los Angeles also has 96 galleries and 36 museums, including the Hammer Museum in Westwood, where a retrospective of Noah Davis’ experimental work runs June 8–August 31, 2025. While there, travelers can book a viewing of the new, appointment-only Grunwald Center for the Graphic Arts. Reserve a table at Lulu, the museum’s onsite, open-air restaurant founded by cookbook author David Tanis and legendary chef Alice Waters.
Visit Joshua Tree National Park
Night falls on Joshua Tree National Park.
Courtesy of Visit California
Heading east of Los Angeles, there are plenty of charming, family-friendly roadside attractions to look out for, from the iconic Donut Hole in La Puente to the massive Cabazon Dinosaurs famously featured in films like Pee-Wee’s Big Adventure. Just be sure to leave ample time to explore the surreal natural features of Joshua Tree National Park, an experience best enjoyed off-road with a private, all-day Red Jeep Tour that will shed some light on the desert’s many mysteries.
See architectural icons in Palm Springs
The new Thompson Palm Springs
Courtesy of Visit California/Winsome Hitchcock
For nearly a century, Palm Springs has been a popular escape for Hollywood’s biggest names, many of whom commissioned renowned architects like Richard Neutra and John Lautner to build their homes in an aesthetic now known as Desert Modernism. To learn more about this influential period in architectural history through a local-led trip through town, Palm Springs Mod Squad offers private, customizable tours to the homes of the likes of Frank Sinatra, Dean Martin, and Marilyn Monroe—all capped off in typical mid-century style with an optional martini. For an up-close glimpse at a new addition to Palm Springs’ proud architectural legacy, a stay at Thompson Palm Springs illustrates how the city continues to chart a distinctive course in modern design.
Check out Malibu’s historic homes
The legendary Santa Monica Pier
Courtesy of Visit California/Max Whittaker
Interstate 10 terminates at Santa Monica, specifically the Santa Monica Pier, a neon-soaked slice of California history that marks the official end point of the world-famous Route 66. Following the coast northwest (with the top down, preferably), Malibu’s Adamson House is a worthwhile stop for docent-led tours through the hacienda, otherwise known as the “Taj Mahal of Tile” for its liberal use of colorful glaze work.
With the right connections, Malibu’s Little Beach House is an art-filled, members-only club where one can rub shoulders with Malibu’s elite. Just a few steps away and dating to 1905, Malibu Pier is a more lowkey experience than its Santa Monica cousin, but is no less iconic. Where else can you fish for thresher shark, shop for designer skateboards and beachwear, or take a whale watching cruise, all from a 780-foot platform over the Pacific?
Drive through Topanga Canyon
Looking at a view of the city from the mountains is a Los Angeles tradition.
Courtesy of Visit California
Going for a drive through Topanga Canyon is scenic enough for its views overlooking the San Fernando Valley, but visiting the local community makes for an authentic California afternoon. Shop for one-of-a-kind Bohemian looks at Moona Star, handmade jewelry and restorative crystals at Jalan Jalan, and vintage clothes at Hidden Treasures. Then, stock up for an unforgettable picnic made up of artisan chocolate, raw cheese, tinned fish, and other specialty groceries from Canyon Gourmet.
Make a unique night of it by digging into a cacio e pepe pizza and sipping natural wine at Endless Color, catching a Shakespearean play at the open-air, historic Will Geer Theatricum Botanicum, and cozying up in a two-person, en suite hot tub at the charming, family-owned Topanga Canyon Inn.
Boat to Catalina Island
Back in Los Angeles’ Westside, Marina del Rey—the largest harbor of its kind in North America—is a lovely place to rent a bike or paddleboard, go birding, or enjoy vegan sushi at Planta Cucina or something more traditional one of the Marina’s many classic waterside restaurants. For a next-level experience, Luxury Liners has a range of yachts that you can charter across Avalon Bay to Catalina Island. It’s a pleasant place to simply enjoy the sea air and unique nature, but be sure to book a VIP Backstage tour of Catalina Casino, an art deco treasure containing a singularly glamorous ballroom that stands out among the many storied sights throughout Los Angeles County.
